187324-66-9

Basic information

• Product Name: PROPIONIC ACID (1R,2S)-2-[N-BENZYL-N-(MESITYLENESULFONYL)AMINO]-1-PHENYLPROPYL ESTER
• Synonyms: Propionic Acid (1R,2S)-2-[N-Benzyl-N-(mesitylenesulfonyl)amino]-1-phenylpropyl Ester (1R,2S)-N-Benzyl-N-(mesitylenesulfonyl)-O-propionylnorephedrine;(1R,2S)-2-[N-Benzyl-N-(Mesitylenesulfonyl)aMino]-1-phenylpropyl Propionate [Reagent for anti-selective asyMMetric aldol reaction];(+)-2,4,6-Trimethyl-N-[(1S,2R)-1-methyl-2-(1-oxopropoxy)-2-phenylethyl]-N-(phenylmethyl)benzenesulfonamide;Masamune reagent;BenzenesulfonaMide,2,4,6-triMethyl-N-[(1S,2R)-1-Methyl-2-(1-oxopropoxy)-2-phenylethyl]-N-(phenylMethyl)-;(1R,2S)-2-(N-Benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl propionate;PROPIONIC ACID (1R,2S)-2-[N-BENZYL-N-(MESITYLENESULFONYL)AMINO]-1-PHENYLPROPYL ESTER
• CAS NO: 187324-66-9
• Molecular Formula: C₂₈H₃₃NO₄S
• Molecular Weight: 479.63
• Product Categories: Asymmetric Synthesis;Synthetic Organic Chemistry
• Mol File: 187324-66-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 149 °C
• Boiling Point: 615.2°C at 760 mmHg
• Flash Point: 325.8°C
• Appearance: /
• Density: 1.163g/cm³
• Vapor Pressure: 4.57E-15mmHg at 25°C
• Refractive Index: 1.578
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: PROPIONIC ACID (1R,2S)-2-[N-BENZYL-N-(MESITYLENESULFONYL)AMINO]-1-PHENYLPROPYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: PROPIONIC ACID (1R,2S)-2-[N-BENZYL-N-(MESITYLENESULFONYL)AMINO]-1-PHENYLPROPYL ESTER(187324-66-9)
• EPA Substance Registry System: PROPIONIC ACID (1R,2S)-2-[N-BENZYL-N-(MESITYLENESULFONYL)AMINO]-1-PHENYLPROPYL ESTER(187324-66-9)

Safety Data

• Hazardous Substances Data: 187324-66-9(Hazardous Substances Data)

Usage

Description

PROPIONIC ACID (1R,2S)-2-[N-BENZYL-N-(MESITYLENESULFONYL)AMINO]-1-PHENYLPROPYL ESTER is a complex ester derivative of propionic acid with a unique molecular structure featuring a benzyl and mesitylenesulfonyl amino group attached to the second carbon of the propionate chain, and a phenylpropyl group at the first carbon. This chemical compound holds potential in the medical and pharmaceutical fields due to its versatile chemical properties.

Uses

Used in Pharmaceutical Industry:
PROPIONIC ACID (1R,2S)-2-[N-BENZYL-N-(MESITYLENESULFONYL)AMINO]-1-PHENYLPROPYL ESTER is used as a prodrug for its potential to be metabolized in the body, releasing the active form of a drug. This characteristic makes it a promising candidate for the development of new pharmaceutical products that can enhance drug delivery and efficacy.
Used in Organic Synthesis:
In the realm of organic synthesis, PROPIONIC ACID (1R,2S)-2-[N-BENZYL-N-(MESITYLENESULFONYL)AMINO]-1-PHENYLPROPYL ESTER serves as a valuable chemical intermediate. Its distinct structure allows it to be a key component in the production of various pharmaceutical compounds, contributing to the innovation of novel therapeutic agents.

InChI:InChI=1/C28H33NO4S/c1-6-26(30)33-27(25-15-11-8-12-16-25)23(5)29(19-24-13-9-7-10-14-24)34(31,32)28-21(3)17-20(2)18-22(28)4/h7-18,23,27H,6,19H2,1-5H3/t23-,27-/m0/s1

Upstream product

• 79-03-8 propionyl chloride 
• 187324-63-6 (1R,2S)-2-[N-benzyl-N-(mesitylenesulfonyl)amino]-1-phenyl-1-propanol 
• 773-64-8 2-mesitylenesulphonyl chloride 
• 108530-02-5 (1R,2S)-2-(N-mesitylenesulfonyl)amino-1-phenyl-1-propanol 
• 492-41-1 (1R,2S)-norephedrine 

Downstream Products

• 694527-59-8 (2R,3R)-3-hydroxy-2-methyltridecanoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)amino]-1-phenylpropyl ester 
• 1416772-51-4 (1R,2S)-2-((N-benzyl-2,4,6-trimethylphenyl)sulfonamido)-1-phenylpropyl(2R,3S,4S)-4-(dibenzylamino)-3-hydroxy-2-methyl-5-(pyridin-3-yl)pentanoate 
• 187324-70-5 (1'R)-phenyl-(2'S)-[(phenylmethyl)[(2,4,6-trimethylphenyl)sulfonyl]amino]-propyl (3R)-hydroxy-(2R),4-dimethylpentanoate 
• 1392284-96-6 ((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) (2R,3R)-6-(tert-butyldimethylsilyloxy)-3-hydroxy-2-methylhexanoate 
• 1354656-85-1 C₄₀H₅₇NO₅S 
• 1333473-58-7 (2R,3R)-[(1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl]-3-hydroxy-4-[(2S,4S,6R)-2-(4-methoxyphenyl)-6-{[(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methyl}-1,3-dioxan-4-yl]-2-methylbutanoate 
• 1180131-47-8 (1R,2S)-2-[benzyl(mesitylsulfonyl)amino]-1-phenylpropyl-(2R,3S,4E)-5-iodo-2,4-dimethyl-3-[(triethylsilyl)oxy]pent-4-enoate 

Relevant articles and documents

Boron-mediated aldol reaction of carboxylic esters: Complementary anti- and syn-selective asymmetric aldol reactions

The boron-mediated aldol reaction of carboxylic esters is described in detail. Contrary to the general belief that carboxylic esters are inert under the condition of the boron enolate formation, propionate esters are enolized with certain combinations of a boron triflate and an amine. More importantly, the stereochemical course of the aldol reaction can be controlled by the judicious selection of the enolization reagents. Treatment of propionate esters with c-Hex2BOTf and triethylamine produces anti-aldol products, and that with Bu2BOTf and diisopropylethylamine gives syn-aldol products selectively after reaction with aldehydes. Complementary anti- and syn-selective asymmetric aldol reactions with structurally related, readily available chiral norephedrine-derived propionate esters are developed.

The anti-selective boron-mediated asymmetric aldol reaction of carboxylic esters

-